Title: Book the Best HISTORIC Hotels in Pittsfield in 2025 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d146411.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/20ffc1c1fd9890df2c042f65a516b89f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Pittsfield, IL from CA $94 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pittsfield Historic Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=146411&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pittsfield Historic Hotels We don't have any properties that match your exact search [See all properties in Pittsfield](https://expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15®ionId=146411&adults=2) ## Recommended hotels in Pittsfield ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (Double Queen Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8f50dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/23a03799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/e9628a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (343) "Small town feel, felt safe walking around at all times of the day. Was in town for a wedding and the location was perfect. AC worked great and beds were comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $113 CA $125 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Comfort Room](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/b4ce7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/47811fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites Pittsfield 9.6/10 Exceptional (57) "Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake CA $164 CA $180 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/c466d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a47c0b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Acres Hotel Pittsfield 8.6/10 Excellent (140) "Best room for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $208 CA $229 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/0aa674c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/13f55165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/74c9995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield 6.8/10 (122) "Quick easy check-in, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $85 CA $94 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/304bbf41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-36d6779a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1080h1437x0y3-5f7123c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-bfee123b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland Pittsfield CA $350 CA $491 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/2e31b21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/w1079h1437x0y3-b96511c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/ab409a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/110000000/109530000/109522400/109522338/70ba5f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake. Pittsfield CA $336 CA $472 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsfield-Hotels-Lovers-Lakeside-Love-Nest-Cozy-Retreat-On-Pittsfields-Serene-Lake.h109522338.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/9e5d5186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/c1c872f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/fcd7f602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12240000/12232200/12232142/48a0e756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River's Edge Motel Louisiana 9.0/10 Wonderful (349) "Clean,quiet, easy parking and great view of the river." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $119 CA $135 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hannibal-Hotels-Rivers-Edge-Motel.h12232142.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/9536012a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/2c8ee78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/50983b3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, Italian cuisine](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/9be9497f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Eagles Nest Inn Louisiana 9.4/10 Exceptional (18) "Clean. Big bathroom. Bed squeaky. Walkable to river and some eating spots. It is full of history and the building was renovated beautifully. There were no common spaces to sit, it would be nice to have that outside of room 11. We would return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $128 CA $146 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Louisiana-Hotels-The-Eagles-Nest-Inn.h111944656.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/b068773a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/22ecf069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/08fef4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/97000000/96130000/96126600/96126590/d2b2608d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy room located in historic downtown with a 5 minute walk to the riverfront! Louisiana 10/10 Exceptional (1) "Great property. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan A. CA $157 CA $195 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Louisiana-Hotels-Cozy-Room-Located-In-Historic-Downtown-With-A-5-Minute-Walk-To-The-Riverfront.h96126590.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w906h683x60y0-f10f078b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w525h683x260y0-46d39fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-6bba3640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w547h683x240y0-d6fb1b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL Jacksonville 10/10 Exceptional (15) "My 2nd stay! I stayed here about 6weeks prior, enroute to visit my daughter at Mizzou. It was so nice that I decided to stay again on my way to her graduation. It was perfect again! It was warm and beautiful in the morning so I even used the outdoor tub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly W. CA $138 CA $176 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15®ionId=146411&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pittsfield Hotel Reviews ![William Watson Hotel](//images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg) ### William Watson Hotel 10/10 Excellent "Great place to stay! Brandi is the best." [](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Pittsfield? > Sights with historical relevance in Pittsfield are probably at the top of your sightseeing list. You can also discover all there is to see and do including the cafes and entertainment choices ### How many historical hotels are located in Pittsfield? > In Pittsfield, there are 10 hotels and other accommodations bookable on Expedia but not many designated as historic hotels. ### What are the top historical places and other sights to visit in Pittsfield? > Landmarks like Pike County Historic Museum and John Greene Shastid House in Pittsfield might be worth a visit. A couple of additional sights to add to your agenda are Old Orchard Country Club and King Park. ### What is a historic hotel like in Pittsfield? > By booking a historic hotel, guests can enjoy a vacation in a place that has a national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features can be admired in the guestrooms or communal spaces of such hotels in Pittsfield, giving a sense of history. ### What is the difference between a historic hotel and a heritage hotel? > You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of historic hotels tend to be what's most significant. For a heritage hotel, it's mainly the cultural value as well as how it inspired the community. ### Do historic hotels in Pittsfield have modern facilities? > Hotels include modern conveniences and safety features you might expect, while every effort is made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found in a hotel will also be available in a historic hotel. 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[Romantic Hotels in Quincy](https://www.expedia.ca/Quincy-Hotels-Romantic-Hotel.0-0-d3622-tRomanticHotel.Travel-Guide-Filter-Hotels) - [B&B in Rockport](https://www.expedia.ca/Rockport-Bed-And-Breakfast.d3000435152-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Rockport](https://www.expedia.ca/Rockport-Hotels-Cheap-Hotels.0-0-d3000435152-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Rockport](https://www.expedia.ca/Rockport-Hotels-Luxury-Hotel.0-0-d3000435152-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Rockport Hotels](https://www.expedia.ca/Rockport-Hotels.d3000435152.Travel-Guide-Hotels) - [Inns in Rockport](https://www.expedia.ca/Rockport-Inns.d3000435152-aaInns.Travel-Guide-Accommodation) - [B&B in Roodhouse](https://www.expedia.ca/Roodhouse-Bed-And-Breakfast.d3000346545-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Roodhouse](https://www.expedia.ca/Roodhouse-Cottages.d3000346545-aaCottages.Travel-Guide-Accommodation) - [Roodhouse Hotels](https://www.expedia.ca/Roodhouse-Hotels.d3000346545.Travel-Guide-Hotels) - 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[Flights from Atlas](https://www.expedia.ca/lp/flights/3000346106/flights-from-atlas) - [Flights from Kampsville](https://www.expedia.ca/lp/flights/553248634983209188/flights-from-kampsville) - [Flights from Bluffs](https://www.expedia.ca/lp/flights/553248634983410026/flights-from-bluffs) - [Flights from Perry](https://www.expedia.ca/lp/flights/553248634983586792/flights-from-perry) - [Flights from Pike County](https://www.expedia.ca/lp/flights/553248635976431336/flights-from-pike-county) - [Atlas Vacations](https://www.expedia.ca/Atlas.d3000346106.Destination-Travel-Guides) - [Visit Atlas](https://www.expedia.ca/Atlas.dx3000346106) - [Visit Benville](https://www.expedia.ca/Benville.dx553248635975847355) - [Car rental Atlas](https://www.expedia.ca/Car-Rentals-In-Atlas.d3000346106.Car-Rental-Guide) - [Car rental Florence](https://www.expedia.ca/Car-Rentals-In-Florence.d553248634983143770.Car-Rental-Guide) - [Greenmotion Drive&Go Rental Cars in Griggsville](https://www.expedia.ca/GreenMotion-DriveGo-Car-Rentals-In-Griggsville.d3000346304-c1042.Car-Rental-Guide-Suppliers) - [Book Historic Hotels in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Hotels-Historic-Hotel.0-0-d146411-tHistoricHotel.Travel-Guide-Filter-Hotels)